Iodoethane → 1-Benzenesulfonyl-2-ethyl-5-(3-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 493154Notes

Reaction equation

HRID 493154 reaction equation
[Li][C:2](C)(C)[CH3:3].CCCCC.[C:11]1([S:17]([N:20]2[C:24]3=[N:25][CH:26]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=4)[CH:28]=[C:23]3[CH:22]=[CH:21]2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(I)C>C1COCC1>[C:11]1([S:17]([N:20]2[C:24]3=[N:25][CH:26]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=4)[CH:28]=[C:23]3[CH:22]=[C:21]2[CH2:2][CH3:3])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8003PentaneHCID 578917421-Benzenesulfonyl-5-(3-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 689517201-Benzenesulfonyl-2-ethyl-5-(3-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridineYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.7 M solution of t-BuLi in pentane (0.71 mL, 1.20 mmol) was added dropwise to a stirred and cooled (−78° C.) solution of 12 (352.0 mg, 1.00 mmol) in THF (2.0 mL). The mixture turned red-brown. After the addition, the mixture was stirred for 30 min at −78° C. Neat EtI (150 μL, 1.88 mol) was added in one portion, and the mixture was allowed to reach 0° C. over a period of 1 h 15 min. The reaction was quenched by the addition of saturated aqueous NaHCO3 solution. The mixture was then extracted with AcOEt (3×3 mL). Combined organic solutions were washed with brine, dried (MgSO4), concentrated and purified by SGC with hexane:AcOEt as eluent in gradient to afford 13 (138.5 mg, 36%) as white solid. 1H NMR (400 MHz, CDCl3) δ 1.42 (t, J=7.3 Hz, 3H), 3.21 (qd, J=7.3, 1.2 Hz, 2H), 6.39 (t, J=1.2 Hz, 1H), 7.07 (dddd, J=8.4, 8.0, 2.5, 1.0 Hz, 1H), 7.25 (ddd, J=9.9, 2.5, 1.7 Hz, 1H), 7.34 (ddd, J=7.7, 1.7, 1.0 Hz, 1H), 7.42 (ddd, J=8.0, 7.7, 5.9 Hz, 1H), 7.46-7.51 (m, 2H), 7.54-7.60 (m, 1H), 7.86 (d, J=2.2 Hz, 1H), 8.15-8.19 (m, 2H), 8.57 (d, J=2.2 Hz, 1H).

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred for 30 min at −78° C
  3. customThe reaction was quenched by the addition of saturated aqueous NaHCO3 solution
  4. extractionThe mixture was then extracted with AcOEt (3×3 mL)
  5. washCombined organic solutions were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. custompurified by SGC with hexane

Sources & evidence

ORD record
ord-2d627847088a4bd89b70041615909aab
Source dataset
uspto-grants-2009_05
Patent number
US07534800B2

Reaction notes

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